If it was me, I'd just bring a basic scanner. I brought my Pro-82 and it worked like a charm. PL tones are nice, but yuo dont need all that fancy stuff at the track.
I went to Bristol.
There are some headphones, they're a cheap brand. I bought two sets for about $20 each. If you plan on attending many races, buy a good set of headphones. I only bought these for Bristol. Your 396T will be a target for scanner-savvy fans. In the large crowds, all one has to do is grab and run.
I will suggest this, go to RadioShack, and buy the small scanner race stub antenna. I think it's like 9.99. It's well worth it. I bought mine, and it came in really handy at the track. It's handy for other things as well. Put it on one of your small scanners, and it will fit into a pocket, without the antenna poking out. Works good for covert scanning too!
I think the headphones I have are "Vanco" brand. They're red, with two seperate volume controls on each ear cup. For light and moderate use, they're very cost effective, and quite comfy. Or they were for me anyway. I'm used to wearing aviation headsets, so these were no problem.
As I said, bring the 92. It has ample memory for each car. The 396, you can program in the driver name as well, but what I did was programmed the frequency into the corresponding car number channel slot. Like Earnhardt Jr, was stored in Memory #8, Jimmie Johnson, in memory #48. That way if I wanted to tune in on a specific driver, all I had to do was hit Manual, 48, and manual again, and the scanner jumped to Jimmie's frequency.
I would just buy the headset at the track. You can order one for a little cheaper, but by the time you SHIP it, you'll be paying about the same money. Buy a quality one though. Like I said, I do like mine, but they're just "basic" headsets. Nothing special.
P.S.- Bring PLENTY of sunblock and drinks to the race as well. $4.00 for a bottle of water is insane... I didn't buy any myself, but I seen the prices and laughed as I walked by with our cooler full of Coke and waters.